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Tips & Resources Travel

How to Plan a Trip For Beginners Pt. 4 – When to Book 


With your awesome itinerary in hand, it’s time to get booking. If you’re wondering, “When’s the right time to book everything?,” well that depends. Are you traveling during high season? Are there few accommodations? So, here’s a few tips when it comes to booking everything for your trip. 

when to book - how to plan a trip for beginners

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When to Book Flights

  • If you’re subscribed to Going (formerly Scott’s Cheap Flights) and you get a deal alert, you’ll want to book as soon as possible. Deals go quickly and sometimes only last 1-2 days.
  • To get the best deals, you have to be flexible with your days. Although you may have plans for a 5 day itinerary, you might find that it’s cheaper to book for 7. 
  • If you’re waiting for a deal, track flights via Google Flights or Hopper. Google Flights will let you know if a price is low, average, or high for your route and time of year. 
  • When it comes to booking flights in between cities, book these once you have your itinerary set. Desirable flight times can sometimes sell out, especially during high season.
  • It’s better to book directly with the airlines vs through a third party. If there’s any complications with your flight, it’s nice to be able to deal directly with the airline. 

Booking Hotels & Accommodations

  • Using Google Maps, I like to save all the locations I’m interested in visiting, and then try to find a hotel near them. 
  • My favorite site to use for booking hotels is If you complete enough bookings, you become a “genius” and unlock different percentages off. 
  • Although I love Booking, sometimes you can find better deals by booking directly through the hotel. For instance, when I stayed at Tabacon in Costa Rica, the hotel had a stay for 2 nights, get the 3rd one free offer.  Check to see if the hotels you’re interested in are offering a deal. If not, book with your site of choice for the loyalty points/status. 
  • If you can, try to book accommodations that have a free cancellation window. Things happen and stuff comes up, and the last thing you want is to not be able to get your money back if you have to cancel. 
  • If you’ll be arriving late to a destination, consider booking a hotel vs an Airbnb. It can be a hassle trying to get in contact with hosts and having them bring you a key late at night. Most hotels have 24 hour check in, which means there’s always someone at the front desk to help you get into your room. 

When to Book Cars, Transfers, and More

  • If you’re renting a car while visiting your destination, book your car as soon as you have your dates. The most affordable rentals tend to be the first to go. Also, if you’re visiting during a popular time and your itinerary is dependent on having a car, you don’t want to chance it on not being able to get one. 
  • Google “renting a car in x destination” to see if there’s anything you need to be aware of. For example, rental companies in Costa Rica are notorious for tacking on extra fees at pick up. You will get one price online but then at pick up, you’ll be hit with a bunch of unforeseen fees.  Just do a quick google so you don’t miss any important tips.
  • Pre-book airport transfers if you’re arriving super late/really early in the morning. Trying to get an Uber at 3:00 AM isn’t the easiest and public transport options are often limited. Check to see if your hotel offers an airport transfer. If not, you can pre-book third-party transfers through Booking or google “X destination airport transfers” to find a service. 
  • Aim to book train journeys about a month before traveling. Again, routes can sell out depending on their popularity and journeys may be limited depending on the time of year. 

Making Restaurant  Reservations

  • If your itinerary is tight, making dining reservations when you can is crucial. Rather than waiting 30 minutes to an hour, you can more so get in and get out. 
  • Check the booking window to see when you can make reservations. Some restaurants open their books months at a time whereas some are only open for a couple of weeks. If the books aren’t open yet, set yourself a calendar reminder. When you get the alert, go in and book. 
  • Sometimes eating at that “once-in-a-lifetime” restaurant means dining at weird times. For an upcoming trip to Spain, my friend and I wanted to dine at Botin, the oldest restaurant in the world. Looking months in advance, the only time available to eat dinner was 3:00 PM. I went ahead and booked it because it’s somewhere we both really wanted to eat. Also, it may be our only opportunity to do so. 
  • If the restaurant you want to eat at doesn’t take reservations, check Google for the estimated wait time and include that in your itinerary plans. Even though you may be going in “low season,” there’s still a chance of a wait if it is a popular place to eat.
when to book restaurants
  • Some restaurants don’t have online booking systems. Look for an email address or number that can be used to make reservations. On the other hand, some restaurants have in-person reservations meaning you’ll have to go physically into the restaurant to reserve a table.
  • DON’T pre-decide EVERY meal you’re going to have unless you’re a serious foodie and you’re trying to specifically hit up certain places. I’ve found that what sounds good while planning the trip doesn’t necessarily always sound good when it comes time to dine. 
  • DO have a list of pre-researched restaurants to cut down on decision making time. I like to have a list of restaurants I looked at and what kind of cuisine they serve so I’m not trying to do this on the ground. This is especially helpful on group trips. I’ve found if you can rattle off a list of restaurants to a group rather than have everyone looking for somewhere to eat, the process goes a lot quicker. 

Booking Tours + Attractions

  • I’m the pre-booking queen. I like to book my attractions as soon as I have a set itinerary. 1. because I don’t have to worry about it selling out and 2. because it’s not an expense I have to worry about when I land. 
  • Some tours and attractions book up early. If you have specific dates and an itinerary all planned out, it’s best to book ahead to avoid any let downs. For instance, when I went to San Francisco, I didn’t get to see Alcatraz. Tickets were available when we first bought our flights but then closer to our date they were completely sold out. 
  • If you don’t have the money this instant but want to secure a ticket, Get Your Guide allows you to reserve now, pay later on certain attractions. You’ll be able to book your attractions, and then your card will be charge a few days before your trip. You can also pay in full anytime after the booking is confirmed. 
  • Viator and Get Your Guide both offer a pay-in-4 solution. This allows you to break the cost of your tours and attractions into 4, interest-free payments. You’ll have to pay the initial quarter up front, and the remaining 3 payments will be taken every 2 weeks.
  • Check for youth and student discounts. If you are under 25 or studying at an EU university traveling within Europe, there are often discounts at major sites and transportation available. For example, you can get reduced admission into Casa Batllo in Barcelona and reduced train fare via Trainline and Rail Europe
  • If you book a tour or tickets through a third-party company like Viator, Get Your Guide or Tiquets, sometimes you will receive a voucher that needs to be redeemed via the official site. When I booked my Kualoa Ranch tickets through Working Advantage, I essentially received a 100% off coupon code. That code then needed to be redeemed on the official Kualoa Ranch website to secure my reservation. Just double-check whether or not there’s anything else for you to do once you book.

Tips for Booking Group Trips

  • I’ve found it’s easier to get people on board for a trip if you can give them basic details upfront. Ticket cost, a rough estimate for rooms, and a couple of highlights is usually good.
  • Google Sheets is a great way to keep track of costs and keep everyone in the budget loop. You can also use Google Docs to get everyone’s input / collaborate on planning your trip.
  • For booking flights, you can hold reservations for your group and then they can call in individually to pay for their ticket. 
  • When booking tours, tickets, hopper flights and trains book them all together. That way everyone’s documents are together in case something happens and someone loses access. PayPal, Apple Pay or Venmo are good for collecting funds.



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